Photo: GKChest · CC BY-SA 3.0232 homes sold in Chesterton in the last year, at a typical $360K
About one sale in 6 is a condo. Below: what each kind of home sells for, what your budget buys, the best months to buy, how hard you’ll have to bid, and a shortcut to every site where Chesterton homes are listed.
Every place Chesterton homes are listed, in one stop
We don’t copy listings: the agents’ sites have the photos and the latest price changes. Set what you want once and we open each site already filtered to Chesterton.
For sale
Rent
New, land & open houses
Links open the listing sites; TownRatings isn’t paid for them and doesn’t rank one above another. Rentals and government-owned homes come from sources outside the MLS.
9% of Chesterton’s sales are condos, at $105K less than a house
181 houses and 21 condos sold in the year to May 2026. Houses sell faster and draw more bidding wars.
typical sale · 181 sold in 12 months
- Per square foot
- $182IN $148
- Days to sell
- 55
- Sold over asking
- 24%
- Listings with a price cut
- 26%
typical sale · 21 sold in 12 months
- Per square foot
- $161IN $160
- Days to sell
- 116
- Sold over asking
- 5%
- Listings with a price cut
- 34%
Multi-family (2–4 units): 14 sold, typical $416K
Townhouses: 16 sold, typical $337K
Too few sales in 12 months for reliable figures.
About as many homes sell as usual, at twice the 2016 price
232 sales in the last year, against 276 in 2021 and a low of 155 in 2012. The typical sale went from $181K in 2016 to $360K.
Source: Redfin Data Center, MLS sales. Typical price and $/sq ft are the monthly medians, weighted by sales.
What $350K buys in Chesterton
Check a listing against what Chesterton homes sold for
Against the town’s median price per square foot over the last 12 months. A rough check: condition, lot and location within town move a price more than this can see.
Bidding wars in Chesterton are more common than before the pandemic, but a quarter fewer homes come up for sale
We read every month of Chesterton’s home sales since 2012 so you don’t have to. Each figure covers 12 months, because a single month in a town is too few sales to mean much. Latest: the year to May 2026, 232 sales.
If you’re buying in Chesterton
- Shop in August. It brings about 28 new listings a month, close to the busiest month, with fewer bidding wars (22% over asking).
- Bid near asking. Buyers paid 99% of the list price on average; 21% paid over.
- You’ll usually have time. Only 39% of homes go under contract within two weeks; the typical one takes 52 days.
Summer brings the homes; spring brings the bidding wars
August has the most new listings (about 28 a month), but April is the most competitive: 27% of April sales close over asking. February has the least competition (15%) but only about 15 new listings.
Averages for each calendar month, 2015 on.
Calmer than the 2021 frenzy, and about like Indiana as a whole
| Chesterton now | 2017–19 | 2021 peak | IN now | |
|---|---|---|---|---|
| Sold over askingShare of sales that closed above the list price | 21% | 13% | 40% | 19% |
| Gone within two weeksShare of homes under contract within 14 days | 39% | 1% | 11% | 37% |
| Listings with a price cutShare of homes for sale that cut their price | 25% | — | 18% | 33% |
| Price paid vs. askingAverage sale price ÷ list price | 99% | 97.6% | 100.6% | 97.7% |
| Days to sellMedian days from listing to contract | 52 | 78 | 49 | 35 |
60 homes for sale on a typical day
That’s 1.6 times the 2023 low (38), 27% fewer than in 2017–19 and well under 2012’s 105.
1 in 4 listings has cut its price
25% in the last year, against — in 2017–19 and 33% across Indiana.
Since 2019, houses are up 68%, condos 94%
A house typically sold for $375K in the last year (181 sales), a condo for $270K (21).
Median sale price, weighted by sales each month. Years with fewer than 4 sales of a type are left out.
Chesterton ranks 50th of 132 busy Indiana markets for bidding wars
Share of sales over asking in the last year, among towns with 60 or more sales. Chesterton is in the middle of the pack.
Source: Redfin Data Center, city market tracker, January 2012 to May 2026 (MLS sales, not seasonally adjusted). Ratios are weighted by homes sold; price cuts by homes for sale.
Owning the typical Chesterton home costs about $2,130 a month
Price: Chesterton’s typical sale, last 12 months. Property tax at Chesterton’s 0.8% (median bill ÷ median value, Census ACS); insurance at 0.35% of price a year. Before PMI, HOA dues, upkeep and the tax deduction. Whether Chesterton is affordable on local pay is on Cost of living.
Six things worth knowing
New listings in August
The month with the most choice. December has the fewest, about 9.
Best time to buyProperty tax, a year
Of a home’s value: the median bill over the median home value. On a $360K home, about $3,030 a year.
Taxes vs. neighborsSchools
The schools grade for Chesterton, from test results, graduation and how much students grow.
Schools in ChestertonTypical commute
The average one-way trip to work for people who live in Chesterton.
Work & commuteCheck the flood map
Flood insurance isn’t in a standard policy, and lenders require it in FEMA flood zones. Check the address before you make an offer.
Natural hazardsLook up any property
Assessed value, lot size and every past sale of a home you’re eyeing are public, at the town or county assessor and the registry of deeds.
South Haven and Portage sell for less a square foot
The busier markets within 25 miles of Chesterton, by what sold. Prices, taxes and how far a paycheck goes next door are on Cost of living.
| Sold | Typical sale | $/sq ft | Over asking | Days to sell | |
|---|---|---|---|---|---|
| Portage | 497 | $292K | $169 | 25% | 39 |
| Chesterton | 232 | $360K | $175 | 21% | 52 |
| South Haven | 76 | $230K | $160 | 22% | 38 |
| Porter | 64 | $303K | $173 | 25% | 36 |
| Burns Harbor | 26 | $341K | $204 | 15% | 76 |
| Ogden Dunes | 25 | $567K | $214 | 16% | 90 |
| Salt Creek Commons | 24 | $239K | $174 | 38% | 38 |
Redfin Data Center, June 2025 to May 2026. Towns with fewer than 20 sales are left out, and Redfin doesn’t report every town separately.
Post your home to Chesterton, free
Selling it yourself, renting out an apartment or looking for a roommate? Post it to Chesterton. People who follow the town see it, and so do people comparing Chesterton with their own town. No commission, no listing fee.
Questions about buying a home in Chesterton
What do homes sell for in Chesterton, IN?
232 homes sold in the year to May 2026 at a typical $360K, $175 a square foot. Houses sold for about $375K, condos for about $270K.
Is Chesterton a buyer’s or seller’s market?
A seller’s market: 41 homes were for sale in May 2026 and 18 sold, about 2.3 months of supply. Buyers paid 99% of asking on average, and 25% of listings cut their price.
When is the best time to buy in Chesterton?
August brings the most new listings. The sales history shows which months have fewer bidding wars.
How much are property taxes in Chesterton?
About 0.8% of a home’s value a year. On a $360K home that’s near $3,030.
Where can I see homes for sale in Chesterton?
Zillow, Redfin, Realtor.com and Homes.com all carry Chesterton’s MLS listings; the search links above open each one filtered to Chesterton.
Sales, prices, days on market and listings: Redfin Data Center (MLS, monthly, not seasonally adjusted). Property tax rate: Census American Community Survey. Two-bedroom rent: HUD Fair Market Rent. Typical home value: Zillow Home Value Index. Schools grade: TownRatings (how grades work).